Nitroguanidine

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Nitroguanidine
Nitroguanidine.svg
Nitroguanidine structure.png
Names
IUPAC name
1-Nitroguanidine
Other names
Picrite
Identifiers
556-88-7 YesY
ChEBI CHEBI:39180 YesY
ChemSpider 10701 YesY
Jmol-3D images Image
PubChem 11174
Properties
CH4N4O2
Molar mass 104.07 g/mol
Appearance Colorless crystalline solid
Density 1.71 g/cm3
Melting point 232 °C (450 °F; 505 K)
Boiling point 250 °C (482 °F; 523 K) (decomposes)
Explosive data
RE factor 1.00
Hazards
Main hazards Explosive
EU Index Not listed
Related compounds
Related compounds
Guanidine
Guanidine nitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Not to be confused with Guanidine nitrate.

Nitroguanidine is an organic compound with the formula (NH2)2CNNO2. It is a colorless, crystalline solid that melts at 232 °C and decomposes at 250 °C. It is not flammable and is a low sensitivity explosive; however, its detonation velocity is high. It is used as a propellant (air bags), fertilizer, and for other purposes.

Manufacture[edit]

Nitroguanidine is produced commercially by a two step process starting with the reaction of calcium cyanamide with ammonium nitrate. Via the intermediacy of biguanidine, this ammonolysis step affords the salt guanidinium nitrate. In the second step, the nitrate salt is treated with sulfuric acid, a process that dehydrates the salt and forms the N-N bond.[1]

[C(NH2)3]NO3 → (NH2)2CNNO2 + H2O

Nitroguanidine can also be generated by treatment of urea with ammonium nitrate. Owing to problems of reliability and safety, this process has not been commerciallized despite its attractive economic features.

Uses[edit]

Explosives[edit]

Nitroguanidine is used as an explosive propellant, notably in triple-base smokeless powder. The nitroguanidine reduces the propellant's flash and flame temperature without sacrificing chamber pressure. These are typically used in large bore guns where barrel erosion and flash are particularly important to avoid.

Pesticides[edit]

Nitroguanidine derivatives are used as insecticides, having a comparable effect to nicotine. Derivatives include clothianidin, dinotefuran, imidacloprid, and thiamethoxam.

Biochemistry[edit]

The nitrosoylated derivative nitrosoguanidine is often used to mutagenize bacterial cells for biochemical studies.

Structure[edit]

Nitroguanidine exists in two tautomeric forms, as a nitroimine (left) or a nitroamine (right). In solution and in the solid state, the nitroimine form predominates (resonance stabilized).[2][3]

Nitroguanidine tautomers.svg

References[edit]

  1. ^ Thomas Güthner, Bernd Mertschenk and Bernd Schulz "Guanidine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_545.pub2
  2. ^ Bulusu, S.; Dudley, R. L.; Autera, J. R. (1987). "Structure of nitroguanidine: nitroamine or nitroimine? New NMR evidence from nitrogen-15 labeled sample and nitrogen-15 spin coupling constants". Magnetic Resonance in Chemistry 25 (3): 234–238. doi:10.1002/mrc.1260250311. 
  3. ^ Murmann, R. K.; Glaser, Rainer; Barnes, Charles L. (2005). "Structures of nitroso- and nitroguanidine x - ray crystallography and computational analysis". Journal of Chemical Crystallography 35 (4): 317–325. doi:10.1007/s10870-005-3252-y.